A computational study of the conformational stability, vibrational spectra, and thermochemical properties of 2,6-dichlorobenzamide, 2-(trifluoromethyl)benzamide, 2-(trifluoromethyl)benzoic acid, and 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid
Author:
Espinosa Manrique Wilfred1ORCID, Badenes María Paula1ORCID, Tucceri María Eugenia1ORCID
Affiliation:
1. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA), Departamento de Química , Facultad de Ciencias Exactas, Universidad Nacional de La Plata, CCT La Plata-CONICET , Casilla de Correo 16, Sucursal 4, (1900) La Plata , Argentina
Abstract
Abstract
2,6-Dichlorobenzamide (BAM), 2-(trifluoromethyl)benzamide (TBAM), 2-(trifluoromethyl)benzoic acid (TBA), and 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid (PCA) are degradation by-products of fluopicolide and fluopyram fungicides. In this work, a detailed theoretical study of their different molecular, spectroscopic and thermochemical properties was carried out with different formulations of the density functional theory and high-level model chemistries. The mean values of −146.0 ± 6.3, −763.2 ± 6.3, −949.0 ± 6.3, and −919.4 ± 6.3 kJ mol−1 for the standard enthalpies of formation of BAM, TBAM, TBA and PCA, respectively, were derived for the first time at the G3MP2//DFT and G4MP2//DFT levels of theory (DFT = B3LYP, BMK, and B98). Additionally, a good agreement between formation enthalpies derived from isodesmic reaction approach and from Benson’s group additivity method was obtained.
Publisher
Walter de Gruyter GmbH
Subject
Physical and Theoretical Chemistry
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